Things to do in Winchester

Find and book activities, attractions and tours

Winchester
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby
Photo by Kelly Godby

Winchester Attractions

They say good things come in small packages, and this endearing city is no exception. From outstanding tourist attractions to thrilling activities, there are countless fun things to do in Winchester.

Discover what makes Winchester tick with some of the very best tours & day trips. Scroll through our {1 fun activities in Winchester fun activities in Winchester}, and book with confidence knowing that we offer free cancellation and no added fees.


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Recommended things to do in Winchester

Number of things to do
1
Cheapest thing to do on Expedia
Shenandoah Tour: Self-Guided Drive: $17
Top 5 things to do
Under $25
With kids

What to do in Winchester

Free Things to Do in Winchester

Vacationing in Winchester on a budget? The following can be experienced for nix.

Jim Barnett Park - If you're hoping to increase the fun factor on your getaway, you can do it here.

Mt Hebron Cemetery - If you'd like to explore the region's history through its landmarks, pencil this one in your travel itinerary.

Handley Regional Library - Organize a visit and learn about the significance of this place to the local community.

Jim Barnett Park - Recharge your mind, body and soul by spending a little time in nature.

Things to Do in Winchester with Kids

There are plenty of fun things to do with your kids in and near Winchester. Keep the gang entertained with our family friendly experiences.


 

Looking for sports, concerts, or theater events in Winchester? Search event tickets to see what's happening today, or to plan what to do this weekend!

 


 


Discover the most popular places to visit in Winchester

Discover the most popular landmarks and neighborhoods in Winchester

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Old Town Winchester

Old Town Winchester is known for its ample dining options, and you can make a stop by Bright Box Theater and Shenandoah Valley Discovery Museum while in the area.

Old Town Winchester
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Winchester Historic District

While visiting Winchester Historic District, you might make a stop by sights like Bright Box Theater and Shenandoah Valley Discovery Museum.

Winchester Historic District

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 


 

Popular day trips from Winchester

Frequently asked questions

Is Winchester worth visiting?
Whether you want to discover the cultural hotspots and local charm or sample unique foods and venture into nature, there's no shortage of things to do in Winchester.
How do I spend a day in Winchester?
Shenandoah Valley Discovery Museum and Appleland Sports Center are two awesome places to begin your sightseeing adventures. Remember to check out the dining and shopping options in Winchester while you're in town too.
What is the top tourist attraction in Winchester?
Don't leave without checking out Shenandoah Valley Discovery Museum, ranked the top tourist attraction in Winchester.
Is three days enough to stay in Winchester?
Three days in Winchester is enough to enjoy the city's main attractions. Many guests spend two days on average. Shenandoah Valley Discovery Museum, Winchester Little Theater and Abram's Delight are highly rated sights. Like to see more? Hang around a while longer to check off nearby hotspots such as Loudoun County.
Is Winchester a walkable city?
With exciting neighborhoods and major attractions within walking distance of the city center, Winchester is a great destination to tour on foot. Have fun wandering between Shenandoah Valley Discovery Museum and Winchester Little Theater. Then take a stroll through Old Town Winchester, located 0.1 miles from the center, and College Park, which is roughly 2 miles away.
What are some activities to do in Winchester with kids?
If you are after tours and attractions for all of your group, take a look at these terrific ideas for what to do in Winchester with kids.
What to do in Winchester for adults?
Valerie Hill Winery and Mt Hebron Cemetery are just a couple of the things to do in Winchester. With loads of activities available, there's something here for everyone to experience.
Are there free things to do in Winchester?
One of the easiest ways to learn about free things to do in Winchester is to ask a local tour guide. You'll get insider advice on exciting neighborhoods, parks and other top attractions you can experience without reaching into your pocket. Mt Hebron Cemetery is one place that doesn't charge an entrance fee.